


Milo and Judith

by WriterMaraMara



Series: Milo and Judith [1]
Category: Original Work
Genre: Anal, Anal Prolapse, Autofellatio, Cock Cleaning, Cock Ring, Collar, Creampie, Eiffel Tower, F/M, Incest, M/M, Prolapse, Restroom, Shemale, Transsexual, Watersports, cumfart, hookup, leash, piss drinking, public, sissy
Language: English
Status: Completed
Published: 2020-04-21
Updated: 2020-04-26
Packaged: 2021-03-01 17:54:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,323
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23761141
Author URL: https://archiveofourown.org/users/WriterMaraMara/pseuds/WriterMaraMara
Summary: Milo is a girly young man with a big dick, and his mother is a pre-op transsexual with a big dick. Can you guess what happens?
Relationships: male/sissy, shemale/sissy, son/mother
Series: Milo and Judith [1]
Series URL: https://archiveofourown.org/series/1711771
Comments: 3
Kudos: 35





	1. Chapter 1

Milo stood at the door to the bathroom, knocking loudly while his legs were bent in together. He had to pee, and he had to do it right now, but his mother was already in there. Milo had been gaming in his room and didn’t have much on, just a black thong that held his huge package and a black tank-top that bared his smooth, svelte midriff. He was a feminine boy, with lips that puckered naturally, big pretty eyes and eyelashes, a round ass that swallowed up his thong, and thighs that could kill. His hair was black and glossy, and getting shaggy as he started growing it out properly. “Mom, c’mon, open up!” He shouted, “I gotta piss! Get up off the toilet or open the door so I can do it in the sink or something!” The door opened, and there was Milo’s mother Judith sitting on the toilet. She puckered her lips up and opened up her mouth at him so she could stick her tongue out and wag it around. “Just do it in my mouth, babe!” 

Milo walked up to her and tugged down on the waistband of his thong undies. His eight-incher flopped out onto Judith’s big tits, and she took hold of it before he could to bring it to her mouth and wrap her lips around it. He sighed and let loose, blasting her mouth with warm, bitter piss that filled quickly at first, then petered down. She swallowed two mouthfuls until he finished, then reached over to the sink and opened up a bottle of mouthwash, pouring it in and swishing around while she wordlessly made a ‘ta-da!’ motion with her hands. 

Judith was in her late forties, almost fifty. Unlike her son, Judith wasn’t so svelte and curvy. What she did have, though, were two huge tits that hung heavily off her chest. That, and a fat cock of her own. Judith was actually a pre-op transsexual. She had been this way since before Milo was born, and when his mother died in childbirth she was more than happy to be his mother and his father. As Milo grew up into adulthood, she became his lover, as well. As it turned out, Milo had become quite the pervert and sexual deviant when she hadn’t been looking, but she was happy to accommodate his needs and desires as long as he did the same for her. Milo tended to be more forceful than Judith about their lovemaking, though. Once he finished pissing, he pulled his cock out of her mouth and slapped it against her tits. “Well since you got my tip wet and your ass is empty, we should fuck,” He said, licking his lips hungrily. 

“I just had an enema, actually,” Judith said, flushing the toilet before getting up and going to the shower, “I’m getting ready for my date with Lucien tonight.” Milo pressed up against her rear as she turned away from him, rubbing his dick between her ass cheeks. He pressed and stroked it up against her loose, raggedy asshole while wrapping his arms around her midsection. “I’ll loosen you up for him, then,” he said as he puckered his lips up and kissed her back, “I only came once today, I’m so horny, mommy.” He could be a brat sometimes, but Judith always liked it when he called her Mommy. 

“Alright, you can fuck me but I want you to pull out before you cum,” she said, “I just cleaned out, after all!” 

Milo quickly pulled his thong and top off and climbed into the shower with her. He got down on one knee behind her and pulled her cheek to the side with one hand so he could lick and tongue at her asshole. It still tasted bitter from her shit, but nothing terrible. His cock quickly grew hard from him stuffing his face into her ass, peaking at just over a foot in length. While his dick would reach deep into her, it wasn’t too thick. She had him beat in girth, and overall he thought she had the manlier cock between them. 

At least no one ever had to get spread out too much to take his dick in them. Once he was hard and her ass was relaxed enough, he poked his shaft up against her asshole. She didn’t really need it, but he did extend the courtesy. Her asshole was loose and hardly able to get tight after years of large insertions of various kinds. Lately, she just wore a plug most of the day to keep anything from leaking out. This meant that Milo could shove most of his dick right up into her shitter and get to pumping before the water even got hot. 

Milo brought his hand down onto her ass, spanking her as he pumped his hips and clapped them into her ass. “Mm, fuckin’ loose-ass bitch,” he said, “Can you even feel me digging around in here?” He shoved his dick in the rest of the way, filling her up and groaning as his head rubbed against the walls of her guts. 

“Of course I can, baby,” she groaned, her own cock hard and jutting out from her waist, “Your dick’s too big to ignore!” Each time he pulled back, it was like he was sucking out something from deep inside her. The best part about getting fucked was that it felt like she was taking a shit that never ended, like she was permanently getting drained and emptied. She started farting, as well, from the air that his cock was shoving back into her. 

“You gross bitch, farting on my dick,” Milo said teasingly, slapping her ass some more, his handprint turning red on her cheek. 

“Don’t call me gross, young man,” she said, “Or you’ll be getting your ass turned out, next!” Despite the threat, Milo seemed to be excited at that because his balls started churning and drawing up in his sack. Soon he was firing out ropes and wads of cum right up into Judith’s ass. Not only that, he was holding onto her hips tight and grinding his hips up into her cheeks while he emptied his balls into. “MILO! Goddammit, you fucking came inside me!” She shouted out angrily. Once he pulled out, she shuddered and farted out an off-white, thick creampie onto the shower floor. “Hey, uh, good thing the shower head comes off the mount,” Milo said, before he quickly hopped out of the shower and ran back to his bedroom, locking his door behind him. 

Despite having just fired off in his mom’s butt, Milo found that he was still horny. He got onto his bed and moved up against the wall, lifting his legs up and bending them back so they fell onto either side of his head. In this position, he could wrap his lips around his own cock and start sucking while stroking his shaft. It tasted dirty, like the inside of his mom’s ass, and he loved it. Reaching over, he grabbed a greasy, unwashed dildo and pushed it into his own ass, slowly working it in and out as his natural anal mucus started to lubricate it, working with the grease to get slippery. Soon his ribbed dildo was popping in and out his ass, making it flutter while he groaned and sucked on his own dick poking and throbbing in his throat. Soon he started to cum again, and this time he wasn’t ready, blowing his load deep into his throat, making him cough and spit up some of the cum, as well as make it run out of his nose. He had to breathe through his mouth for a while until he was able to blow all the cum out of his nose. His mom had left by then to go on her date, but she’d be back eventually.


	2. Park Restroom Fun

One could tell from this previous encounter that Judith could be a piss pig from time to time. The truth is that she was teaching Milo to be the same, but she wasn’t some overbearing domme that was on top of him all the time. She would pressure or force him into such situations when she felt like it, once or twice a week.  


Today was one of those days, where she went to the living room to find Milo on his phone. He was dressed in a loose sweater, a skirt that went to his knees, and kneesocks. Judith was dressed in a low-cut, long-sleeved top and a long skirt, with pantyhose underneath. She had in her hand a spiked dog collar, which she dropped onto Milo’s chest. “Come on, baby, we’re going for a walk,” she said, as she held up her hand to wiggle a leash she had brought with. Milo looked up at her with a look that said he was thinking about whether he wanted to go or not, but she won out on him and he quietly put the familiar collar on.  
Once the collar was on, Judith pulled him in close to her silicone tits and squeezed him tightly. She ran her hands over his head, petting him and his hair while she asked, “Who’s mommy’s pretty puppy?” In an overly motherly tone.  


“I’m mommy’s pretty puppy,” Milo said, breathing in her smell while his face was pressed into her cleavage. She let go of him after a moment, then brought out from her skirt pocket a silicone cock ring.  


“Here, so you’re not getting so perky during our walkie.” Milo took it from her and squatted down, pulling his skirt up so he could take hold of his cock and pull the ring down to his base, then carefully pull his balls through. Whether it was his mother’s intention or not, he was semi-hard by the time it was properly on, and tenting his skirt. He didn’t wear underwear, of course.  


The pair lived in a two-story house across from a sizable park. It was the pride of the town they lived in because it was so large, despite the town being of average size. It had a long jogging trail and plenty of trees and foliage, so the local perverts such as our pair were quite fond of coming there. Judith pulled on his leash to bring him across the street with her, before they went walking on their usual path. Judith liked to go at a pace that was more than Milo usually walked at. She was more fit than he was, so it was a treat that soon enough he was panting to keep up like a little puppy. He didn’t say anything, though, because he knew that she would tease him for not keeping in shape and just being a ‘skinny faggot,’ as she liked to call him.  


After about half an hour, they came to their usual bench for these walks and sat down, Judith first. Milo sat with some space between them, making the leash quite obvious. Their routine here was that Judith would pull out her phone and start reading, while Milo would sit with his legs open to allow someone to see up his skirt. If anyone showed interest, then they’d go to a public restroom not too far away.  


Milo usually wasn’t prepared for these walks, so he’d get really bored before too long. He’d zone out until someone would come by, and usually they’d pass right on rather than sit across from these two weirdos. Milo closed his eyes and started to doze off, until he noticed someone sitting next to him. It was a man who looked to be in his mid-40s, overweight, balding, wearing shorts and a t-shirt that didn’t match. “Hey there, honey,” he said, putting his hand on Milo’s thigh and running it up and down, “Is that your mistress over there?”  


“Actually, she’s my mommy,” Milo said, “Why do you ask?”  


“I thought I’d see if I could get to know you two,” the guy said, his hand going in between Milo’s legs, finding his dick and squeezing it. He seemed excited at the size Milo was packing in this semi-hard state.  


Judith turned to look over at them, then clucked her tongue and whistled to get their attention. “Hey stranger, if you wanna do something we can do it in private,” she said, then nodded towards the nearby restroom. He got up, his cock hard in his shorts. Milo checked it out and sized it up, estimating it to be a bit more than average. Together, the three went up the hill to the restroom and went inside. There was no light inside, just natural light that shone through frosted glass. Judith brought a padlock with her and used it to keep the door shut while they carried on inside.  


While Judith was busy with that, the pair’s new friend was squatting down so he could yank down Milo’s skirt. The sissy’s cock hung in a semi-hard state, its prodigious length and dark skin making it look absolutely delectable. The pervert licked his lips and took it into his mouth, sucking it in and trying to deepthroat it. He did an alright job, but didn’t seem to be very experienced. Not with lengths of Milo’s size, at least. Judith came up to them and stood behind the man, unzipping the side of her skirt and letting it fall to the floor. She stood with her legs spread, stroking her thicker cock slowly while looking at the two. She pulled back her foreskin over and over, baring and hiding her pink head among her darker foreskin. Her tongue stuck out and licked her lips while she looked at her baby boy getting his cock sucked.  


Milo was up against the wall between two urinals he had his elbows propped up onto. The man pulled his mouth off his cock, leaving it covered in spit and throat slime. Milo’s dick was still semi-hard, unable to get any further thanks to the cock ring around his base, stuck in a partially floppy state. The man stuffed two fingers into his mouth to get them wet, then slid them up Milo’s ass to cram them up into his backdoor. Milo groaned loudly, not expecting the sudden and rough insertion. The guy’s nails weren’t well-cut, he probably bit them. The man worked his fingers around inside, pressed against Milo’s developed prostate gland and massaged it. He sucked Milo’s cock back into his mouth, going down deep on him again while gagging intermittently. “Having a good time, honey?” Judith asked, as her cock stood at full hardness. She was spurting out pre-cum in ropes and squirts that splattered onto the man’s back, though he didn’t seem to notice.  


“It’s something, alright,” Milo said. This was pretty embarrassing for him, getting sucked off by such an average looking guy but still enjoying it as much as he was. The fingers were doing most of the work, and his butthole was clenching and squeezing on them, sucking them like a dick while they prodded his p-spot.  


Milo busted his nut after about ten steady minutes of fingering. He tapped the guy’s shoulder to let him know, and the guy pulled back so he could just cum inside his mouth. The stranger grunted and snorted loudly so that he sounded like a pig. He squealed with delight as his mouth filled with cum, splashing around and filling the nooks and crannies of his gums. He pulled back before Milo finished, so the young sissy finished cumming by squirting a couple ropes right onto the guy’s shirt while he sat back and swirled it around in his mouth. He kept grunting and squealing, then opened his mouth to show Milo all the cum he was gargling. “That’s nice,” Milo said.  


Judith helped the guy up onto his feet, then turned Milo around to face the wall. She slapped his ass and spread his cheeks out, showing his less-than-tight asshole. “How’d you like to fuck my baby girl’s pussy?” She asked, while she slapped her cock against Milo’s ass cheeks, “Then I can get your sloppy seconds while you watch.” The guy agreed to it wordlessly, dropping his shorts and getting right up against Milo’s ass with his gut and cock. He jabbed and poked against his asshole a couple times, trying to get it in blindly until he found his mark and thrust in.  


While his size overall wasn’t impressive, he could fuck at a good pace. With his hands on Milo’s hips, he pounded up against his round butt hard and loud enough to fill the bathroom with the sound of his clapping. Milo was now groaning actively as his asshole was turned to jelly, loosening up and starting to fart around the guy’s dick from the air that was getting pushed in and forced out. He leaned forward to kiss Milo’s neck, and sucked on it hard enough to leave a few hickeys. He smelled like Ralph Lauren cologne up close.  


Judith pulled her sweater up so she could paw at her own tits while she stroked her cock, watching Milo get fucked. She rubbed her dick between them, squirting her pre-cum onto the ‘lovers’ as she watched and waited for her turn. “Mm, how’s my baby girl’s pussy, piggy?” She asked, tracing her finger over the guy’s jawline, “You gonna cum soon?”  


As if by magic, the guy crammed his cock in and held still while he fired off into Milo’s bum. Two modest squirts flew up into Milo’s guts, nothing spectacular. He ground around inside a while more, then pulled his flaccid cock out. Judith gave him a few pats on the rump and directed him to walk away, while she mounted up behind Milo and had her turn. Cum and anal mucus was drooling out of his butt, but she quickly plugged it up with her head before jamming her whole cock deep into him.  


Judith’s dick wasn’t very long, but it was thick. He was always stretched out when his mommy fucked him. While he had been groaning from getting fucked by the randy guy, he was now in a full-on state of moaning deeply while his legs wobbled and clapped together. Judith’s fat cock sawed in and out of him, making his asshole open up and bloom around it. Judith grabbed him by the neck and spun around with him to face the stranger, then bent him over. “Clean his cock off,” she said, “It’s only polite.”  


The guy took hold of Milo’s head and pulled him down the rest of the way to get his dick sucked clean. He held Milo’s head in place while he was licked at, but soon ended up pissing into Milo’s mouth. He was barely able to swallow it in time while being fucked by Judith, but he knew he’d face some kind of punishment if he spilled any and this was getting gross enough for him. He swallowed down the bitter, warm piss while groaning and shuddering from the hard, heavy fucking his mommy was giving him.  


When Judith blew her load, it was deeper inside and much more impressive in terms of volume. Rope after rope of sticky cum flew up and splattered inside him, filling the last corner of his digestive tract up with warm baby batter. When she pulled out, he let out the sloppiest cumfart anyone ever heard, and on top of that his asshole bloomed into a rosebud.  


The stranger thanked Judith while almost ignoring Milo, and left quickly. Judith didn’t stay for long, either, and pulled Milo along and out of the restroom. Milo had to walk back home on a leash, with weak legs and his ass farting with every other step while oozing out cum from his prolapsed asshole. And to be honest, he loved it.


End file.
